Veratraldehyde → HCID 69203091, compound

HRID 2378173Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:7].Br[C:14]1[CH:23]=[CH:22][C:17]2[O:18][CH2:19][CH2:20][O:21][C:16]=2[CH:15]=1.C([Li])CCC.O1C2C=CC(C(C3C=C(OC)C=C(OC)C=3)O)=CC=2OCC1>>[O:11]1[C:10]2[CH:9]=[CH:8][C:5]([CH:6]([C:14]3[CH:23]=[CH:22][C:17]([O:18][CH3:19])=[C:16]([O:21][CH3:20])[CH:15]=3)[OH:7])=[CH:4][C:3]=2[O:2][CH2:1][CH2:12]1

Participants

Reactant 4

HCID 8419Veratraldehyde

HCID 1041416-Bromo-1,4-benzodioxane

HCID 69202534(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol

HCID 178418339Butyllithium

Product 1

HCID 69203091HCID 69203091, compoundYield 89.4%

Procedure

3,4-dimethoxybenzaldehyde (2.21 g, 13.32 mmol), 6-Bromo-2,3-dihydrobenzo[1,4]dioxine (3.15 g, 14.65 mmol), and n-butyl lithium (5.86 ml, 14.65 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.) to give (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(3,4-dimethoxy-phenyl)-methanol as an oil (3.60 g, 89%): 1HNMR (CDCl3) 6.93-6.80 (m, 6H, Ar), 5.70 (d, J=3 Hz, 1H, CHOH), 4.24 (s, 4H, CH2CH2), 3.86 (s, 6H, 2OCH3), 2.14 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Workup

customThe crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.)

Sources & evidence

ORD record: ord-54e007fd48924eb0be0e3de8abe15af6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470723B2

Reaction notes

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